Upper Matecumbe Key Travel Guide

Tourist Guide

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
A pier extending into calm waters with a covered seating area and a sandy beach.
A pelican standing on a wooden dock.
A pier with birds perched on poles, a sign, and a bridge in the background.
A calm lake with a reflection of trees and a cloudy sky.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is £176 per night from 1 Sept to 2 Sept
£176
1 Sept - 2 Sept
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is £167 per night from 26 Aug to 27 Aug
£167
26 Aug - 27 Aug
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is £178 per night from 24 Aug to 25 Aug
£178
24 Aug - 25 Aug
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,291 reviews)
"Let’s see, loud neighbors, dirty pool, small rooms, hot lobby. True tourist hotel."

Reviewed on 2 Aug 2026

Amara Cay Resort
See all 2,776 properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
Breezy Palms Resort
Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada FL
Stay at this cottage in Islamorada. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (117 reviews)
"Host was very responsive when we reached out and the place had everything we needed. The dock for the boat was very easy to get in and out of and we had plenty of room for the trailer. The place was also very clean."

Reviewed on 11 Jun 2026

Oceanfront Private Cottage!
Oceanfront Estate - Private Beach, Pool, & Dock

Oceanfront Estate - Private Beach, Pool, & Dock

Islamorada FL
Stay at this beach holiday home in Islamorada. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Bud n' Mary's Dive Center and Hurricane ...
10/10 Exceptional! (4 reviews)
"Our family of 10 recently stayed at this wonderful home for one week. The property was large enough to easily accommodate our group. The views are stunning, the pool and grounds are very nicely done. The screened lanai was great for extended evenings outside without worrying about bugs. Well maintained ..."

Reviewed on 22 Jun 2026

Oceanfront Estate - Private Beach, Pool, & Dock
See all properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.
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Cities near Upper Matecumbe Key

A beach with palm trees and white lounge chairs under a clear blue sky.

Islamorada

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